3-(chloromethyl)-2,5,6-trimethyl-1H,7H-[1,2]diazolo[1,2-a]pyrazole-1,7-dione

• ChemBase ID: 133593
• Molecular Formular: C10H11ClN2O2
• Molecular Mass: 226.65954
• Monoisotopic Mass: 226.05090528
• SMILES: Cc1c(n2c(c(c(=O)n2c1=O)C)CCl)C
• Canonical SMILES: ClCc1c(C)c(=O)n2n1c(C)c(c2=O)C
• InChI: InChI=1S/C10H11ClN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
• InChIKey: SUIPVTCEECPFIB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(chloromethyl)-2,5,6-trimethyl-1H,7H-[1,2]diazolo[1,2-a]pyrazole-1,7-dione
• IUPAC Traditional name: monochlorobimane
• Synonyms: Chlorobimane; Chlorobimane; Monochlorobimane

Database IDs

• CAS Number: 76421-73-3
• MDL Number: MFCD00077379
• Beilstein Number: 4440901
• PubChem SID: 162227870; 24892698; 24886000
• PubChem CID: 114886

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.9230597
• LogD (pH = 7.4): 0.9230597
• Log P: 0.9230597
• Molar Refractivity: 58.8005 cm^3
• Polarizability: 21.529467 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble; DMF: soluble; DMSO: soluble; methanol: soluble
• Melting Point: 135-136 °C(lit.)
• Fluorescence: λex 380 nm; λem 461 nm in methanol; λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPCE)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C10H11ClN2O2

DETAILS

Sigma Aldrich - 69899

Application
Cell-permeant probe for quantifying glutathione levels in cells.1 Suitable for the detection of thiol-groups.
General description
Contains up to 15% of an isomer (NMR)